Unusual borane addition to conjugated dienylphosphanes under frustrated Lewis pair conditions.
نویسندگان
چکیده
Dimesitylphosphinoisoprene 9a reacts with a series of R-B(C6F5)2 boron Lewis acids by isomerization and subsequent 1,4-P/B addition to give the heterocyclic phosphonium/borate zwitterionic products 13. Subsequent hydride abstraction from the isoprenyl derived methyl group by trityl cation proceeds with elimination of the R-B(C6F5)2 reagent to give the heterocyclic phosphonium system 20.
منابع مشابه
Geminal bis-borane formation by borane Lewis acid induced cyclopropyl rearrangement and its frustrated Lewis pair reaction with carbon dioxide.
Cyclopropylacetylene reacts with two molar equivalents of Piers' borane [HB(C6F5)2] under mild conditions by an addition/rearrangement sequence with cyclopropyl ring opening to give a mixture of two α-B(C6F5)2 substituted tetrahydroboroles. This compound forms an active frustrated Lewis pair with P t Bu3 that heterolytically splits dihydrogen and adds carbon dioxide as a geminal chelate bis-bor...
متن کاملGeminal bis-borane formation by borane Lewis acid induced cyclopropyl rearrangement and its frustrated Lewis pair reaction with carbon dioxide† †Electronic supplementary information (ESI) available: Experimental and analytical details are given. CCDC 1487577–1487584. For ESI and crystallographic data in CIF or other electronic formats see DOI: 10.1039/c6sc03468c Click here for additional data file. Click here for additional data file.
Cyclopropylacetylene reacts with two molar equivalents of Piers' borane [HB(C6F5)2] under mild conditions by an addition/rearrangement sequence with cyclopropyl ring opening to give a mixture of two a-B(C6F5)2 substituted tetrahydroboroles. This compound forms an active frustrated Lewis pair with PBu3 that heterolytically splits dihydrogen and adds carbon dioxide as a geminal chelate bis-boryl ...
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Reactions of a frustrated Lewis pair composed of a sterically encumbered phosphine and borane are shown to react with 1,3-dienes to give the 1,4-addition products.
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The activation of π-bonds in diynyl esters has been investigated by using soft and hard Lewis acids. In the case of the soft selenium Lewis acid PhSeCl, sequential activation of the alkyne bonds leads initially to an isocoumarin (1 equiv PhSeCl) and then to a tetracyclic conjugated structure with the isocoumarin subunit fused to a benzoselenopyran (3 equiv PhSeCl). Conversely, the reaction with...
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The dienylborane 2a was prepared by regioselective alkyne hydroboration of the conjugated enyne 1a with Piers' borane [HB(C6F5)2]. Its reaction with a series of acetophenone derived enamines 3 resulted in the formation of the strong enamine β-carbon adduct with the borane Lewis acid (4). In contrast B-C adduct formation between the dienylborane 2a and a series of much more bulky cyclohexanone d...
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ورودعنوان ژورنال:
- Dalton transactions
دوره 45 14 شماره
صفحات -
تاریخ انتشار 2016